Sodium Hydroxide → 2-Nitrothieno[2,3-b]pyridin-3-amine

HRID 1615665Notes

Reaction equation

HRID 1615665 reaction equation
[SH:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH-].[Na+].Br[CH2:13][N+:14]([O-:16])=[O:15]>CN(C=O)C.O>[N+:14]([C:13]1[S:1][C:2]2=[N:9][CH:8]=[CH:7][CH:6]=[C:3]2[C:4]=1[NH2:5])([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 68423BromonitromethaneHCID 178510023HCID 178510023, compound

Product 1

HCID 131693742-Nitrothieno[2,3-b]pyridin-3-amineYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-mercaptonicotinonitrile (1 g, 7.4 mmol) in DMF (20 mL) was added a solution of NaOH (0.88 g, 22 mmol) in water (5 mL) at 0° C. The mixture was stirred for 20 min, then bromonitromethane (2 g, 14.7 mmol) was added dropwise. The resulting mixture was stirred for 1 h at 0° C., diluted with water (100 mL), and filtered. The filter cake was washed with water (20 mL×3) to give a yellow solid (1.1 g, yield 78%), which was used in the next step without further purification. ESI MS: m/z 196 [M+H]+.

Workup

  1. stirringThe resulting mixture was stirred for 1 h at 0° C.
  2. filtrationfiltered
  3. washThe filter cake was washed with water (20 mL×3)

Sources & evidence

ORD record
ord-3ebc0111121944e7913999c4d597dfc2
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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